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WO2018164777A1 - Résine hydrocarbonée fonctionnalisée par un groupe polaire par modification post-réacteur - Google Patents

Résine hydrocarbonée fonctionnalisée par un groupe polaire par modification post-réacteur Download PDF

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Publication number
WO2018164777A1
WO2018164777A1 PCT/US2018/015370 US2018015370W WO2018164777A1 WO 2018164777 A1 WO2018164777 A1 WO 2018164777A1 US 2018015370 W US2018015370 W US 2018015370W WO 2018164777 A1 WO2018164777 A1 WO 2018164777A1
Authority
WO
WIPO (PCT)
Prior art keywords
polar
phr
resin composition
rubber
functionalized resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2018/015370
Other languages
English (en)
Inventor
Ranjan Tripathy
Jason A. MANN
Edward J. Blok
Thomas R. Barbee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Chemical Patents Inc
Original Assignee
ExxonMobil Chemical Patents Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ExxonMobil Chemical Patents Inc filed Critical ExxonMobil Chemical Patents Inc
Priority to KR1020197026404A priority Critical patent/KR20190120768A/ko
Priority to CN201880026318.3A priority patent/CN110770263A/zh
Priority to EP18704383.1A priority patent/EP3592785A1/fr
Priority to SG11201908246W priority patent/SG11201908246WA/en
Priority to JP2019548678A priority patent/JP2020514501A/ja
Priority to US16/491,260 priority patent/US20200010595A1/en
Publication of WO2018164777A1 publication Critical patent/WO2018164777A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/08—Epoxidation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/26—Incorporating metal atoms into the molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
    • C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
    • C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
    • C08F4/14—Boron halides or aluminium halides; Complexes thereof with organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/06—Oxidation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/14—Esterification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups

Definitions

  • This invention relates to a polar functionalized hydrocarbon resins and processes to produce thereof.
  • Acrylic adhesives are widely used as hot melt adhesives, heat activatable adhesives, and pressure-sensitive adhesives.
  • substrates such as certain types of automotive paints and low energy olefinic surfaces, to which typical acrylic adhesives do not adhere well.
  • Efforts have been made to improve the adhesion of acrylic adhesives, i.e., develop more aggressive tack, to these types of surfaces; tackifying the base acrylic polymer is commonly practiced.
  • Various types of tackifying resins such as phenol modified terpenes and rosin esters, are used as tackifiers.
  • Hydrocarbon resins have been used as modifiers for coatings (corrosion-resistant lacquer), reactive adhesives (two-pack epoxy or polyurethane) and integrated circuit encapsulants (epoxy resin based) as they are capable of plasticizing base polymers, relaxing the internal stress generated during the curing of base polymers, increasing the initial tack and adhesive strength of base polymers, and improving water resistance of base polymers.
  • the modifying effects produced by such hydrocarbon resins however, have not been too satisfactory. In particular, they are not applicable to strongly polar base polymers because of their poor compatibility.
  • an aim of this invention is to solve the above-mentioned issues of conventional hydrocarbon resins.
  • Another objective of the present invention is to synthesize high performance tire treads possessing exceptional traction and handling properties.
  • miscible hydrocarbon resins are typically used in tread compound formulations in order to increase traction characteristics. Although these resins increase overall traction, tread compounds formulated with these miscible resins tend to suffer from reduced traction and handling at high speeds or at high internal tire generated temperatures during hard driving. The foregoing and/or other challenges are addressed by the methods and products disclosed herein.
  • This invention relates to a process for the preparation of a polar-functionalized resin composition
  • a process for the preparation of a polar-functionalized resin composition comprising the steps of (A) contacting a polymer backbone with a reactive moiety to produce a polar-functionalized resin composition, wherein the polymer backbone is derived from a feed comprising less than or equal to about 35 wt% components derived from piperylene; less than or equal to about 10 wt% components derived from amylene; less than or equal to about 10 wt% components derived from isoprene; less than or equal to about 55 wt% unreactive paraffins; and C9 homopolymer or copolymer resins, in the presence of a Friedel- Crafts or Lewis acid catalyst; and (B) recovering a polar-functionalized resin composition.
  • Figures 1 to 5 depict the proton NMR charts for inventive polar functionalized hydrocarbon resins of the invention.
  • phr means parts per hundred parts of rubber, and is a measure common in the art wherein components of a composition are measured relative to the total of all of the elastomer (rubber) components.
  • the total phr or parts for all rubber components, whether one, two, three, or more different rubber components when present in a given recipe, is always defined as 100 phr. All other non-rubber components are ratioed against the 100 parts of rubber and are expressed in phr.
  • interpolymer means any polymer or oligomer having a number average molecular weight of 500 or more prepared by the polymerization or oligomerization of at least two different monomers, including copolymers, terpolymers, tetrapolymers, etc.
  • monomers in an interpolymer is understood to refer to the as-polymerized and/or as-derivatized units derived from that monomer.
  • polymer and interpolymer are used broadly herein and in the claims to encompass higher oligomers having a number average molecular weight (Mn) equal to or greater than 500, as well as compounds that meet the molecular weight requirements for polymers according to classic ASTM definitions.
  • the functionalized resin molecules of the present invention are prepared via post- reactor treating of a polymer backbone.
  • polymer backbone includes substituted or unsubstituted units derived from Cs fraction homopolymer or copolymer resins, C9 fraction homopolymer or copolymer resins, and combinations thereof.
  • resin molecule or “resin” as used herein is interchangeable with the phrase “polymer backbone.”
  • the polymer backbone comprises up to 100 mol% units derived from C5 fraction homopolymer or copolymer resins, more preferably within the range from 5 to 90 mol% units derived from C5 fraction homopolymer or copolymer resins, most preferably from 5 to 70 mol% units derived from C5 fraction homopolymer or copolymer resins.
  • the feed leading up to the polymer backbone comprises up to 35% piperylene components, up to 10% isoprene components, and between 5 to 10% amylene components by weight of the monomers in the monomer mix.
  • C9 refers to a petroleum distillate containing styrene, indene, alkyl derivatives, and combinations thereof.
  • the polymer backbone has a refractive index greater than 1.5.
  • the polymer backbone has a softening point of 80°C or more (Ring and Ball, as measured by ASTM E-28, with a heating/cooling rate of 10°C/min) more preferably from 80°C to 150°C, most preferably 100°C to 150°C.
  • the polymer backbone has a glass transition temperature (Tg) (as measured by ASTM E 1356 using a TA Instruments model 2920 machine, with a heating/cooling rate of 10°C/min) of from -30°C to 100°C.
  • Tg glass transition temperature
  • the polymer backbone has a Brookfield Viscosity (ASTM D-3236) measured at the stated temperature (typically from 120°C to 190°C) using a Brookfield Thermosel viscometer and a number 27 spindle of 50 to 25,000 mPa-s at 177°C.
  • ASTM D-3236 Brookfield Viscosity
  • the polymer backbone comprises olefinic unsaturation, e.g., at least 1 mol% olefinic hydrogen, based on the total moles of hydrogen in the interpolymer as determined by !fl-NMR.
  • the polymer backbone comprises from 1 to 20 mol% aromatic hydrogen, preferably from 2 to 15 mol% aromatic hydrogen, more preferably from 2 to 10 mol% aromatic hydrogen, preferably at least 8 mol% aromatic hydrogen, based on the total moles of hydrogen in the polymer.
  • polymer backbones useful in this invention include Escorez® 8000 series resins sold by ExxonMobil Chemical Company in NDG, France. Further examples of polymer backbones useful in this invention include Arkon® series resins sold by Arakawa Europe in Germany. Yet more examples of polymer backbones useful in this invention include the Eastotac® series of resins sold by Eastman Chemical Company in Longview, TX.
  • the initial polymerization of steam-cracked petroleum hydrocarbons may be carried out in any conventional batch, semi-continuous or continuous fashion, all of which are well known in the petroleum resin art.
  • the desired unsaturated hydrocarbon mixture is preferably contacted with small amounts of Friedel-Crafts catalyst such as boron trifluoride, aluminum chloride, aluminum bromide or the like. Amounts of such catalyst from 0.25 to 3.0% based on the unsaturated content of the feed are preferred.
  • the catalyst may be employed in its solid state or in solutions, slurries or complexes.
  • boron trifluoride may be complexed with ether to form an etherate in accordance with techniques known in the art and the etherate may be employed as the catalyst.
  • the polymerization reaction is conducted with temperatures in the range of -30 to 90°C, and preferably from 0 to 75°C.
  • an inert diluent such as benzene, naphtha, paraffins, cycloparaffins or other hydrocarbon fractions preferably boiling in the range of 70 to 125°C.
  • the diluent may be employed in amounts from 5-75 by weight based on the olefin-containing feed.
  • the diluent may be added first, last or at the same time as the feed.
  • the reactor should comprise means for agitating the reaction mixture and the feed is preferably agitated during the addition of the catalyst and during the entire reaction time.
  • the catalyst is added slowly over a period of 5 minutes to one hour or until the desired catalyst concentration has been reached.
  • the temperature of the reaction mixture may be controlled by any known technique, a particularly preferred one is referred to normally as a pumparound system where the reaction mixture is continuously circulated through a temperature-controlling bath adapted to either heat or cool the mixture. After the start up on the reaction, the catalyst is continuously added at a rate to give the desired catalyst concentration together with fresh steam-cracked hydrocarbon feed. In a continuous system, a portion of the reaction mixture is continuously drawn off to a second vessel if desired to provide additional contact time and the product is withdrawn from the second vessel either batchwise or continuously.
  • One technique for carrying out a batch reaction comprises forming a slurry of the catalyst in diluent and then slowly adding the steam cracked feed. The mixture is continuously agitated. If desired, only a portion of the aluminum chloride is added initially and the remainder after the reaction is started. The product mixture is then quenched, washed and stripped to give the final resin product.
  • the reaction mixture may be quenched with an acid such as dilute sulfuric or phosphoric acid to stop the reaction. Water soluble non-ionic wetting agents such as alkyl polyethers, etc. may also be employed. These are all well known in the art. Subsequent to the quench, the product is usually water and/ or alkali washed to remove any residual acidity.
  • the resin solution is then stripped of diluent, unreacted hydrocarbon and any low molecular weight polymer to give the hard resin product.
  • the stripping may be carried out in accordance with well-known techniques by vacuum or steam distillation.
  • hard resins are conveniently recovered by stripping to a bottoms temperature to about 270°C at 2-5 mm. Hg or the solution may be steam stripped for about 2 hours at 260°C. While the softening point may be raised by increasing the severity and/ or time of stripping, this only results in relatively small increases in softening point and is accompanied by a loss in resin yield with a corresponding increase in undesired liquid polymer.
  • the polymer backbone used in the present invention may also be prepared by thermal polymerization methods known in the industry.
  • the backbone may be prepared by thermally polymerizing steam cracked petroleum hydrocarbons in a thermal polymerization unit known in the art to achieve a desired molecular weight and composition. After processing in a thermal polymerization unit, the backbone may be nitrogen or stream stripped to prepare for functionalizing.
  • the resin is then functionalized.
  • the functionalization of the backbone after polymerization is referred to herein as "post-polymerization” or "post-reactor.”
  • the backbone is functionalized by reacting it with a reactive moiety.
  • the moiety is a polar compound selected from the following: pero-oxy acids, hydroboration agents, acetylation agents, thiols, and combinations thereof.
  • the percent of polar units in the polar- functionalized resin composition is in the amount of about 10 to about 15 mol% based on the composition.
  • the functionalized polymer produced by this invention can be used in water borne emulsion adhesives, reactive adhesives and sealants, and high performance tire tread compositions.
  • the high performance tire tread composition is formed by blending the polar- functionalized polymer produced by this invention with diene elastomer and inorganic filler.
  • the silica treated functionalized polymer is present within the range from 5 to 100 phr, more preferably 10 to 50 phr.
  • the diene elastomer may comprise a blend of two or more elastomers.
  • the individual elastomer components may be present in various conventional amounts, with the total diene elastomer content in the tire tread composition being expressed as 100 phr in the formulation.
  • the inorganic filler is present within the range from 50 to 150 phr, more preferably 50 to 100 phr, most preferably 60 to 90 phr.
  • the water borne emulsion adhesive composition is formed by blending about 100 phr of acrylate/vinyl acrylate polymer, about 10-50 phr of the polar-functionalized polymer (preferably Resin C or D, described below), about 10-50 phr of additives, and about 5 to 30 phr of water.
  • the reactive adhesive or sealant composition is formed by blending about 5-100 phr of polar-functionalized polymer (preferably Resin B described below), about 5-75 phr of polymer or monomeric amine or anhydride to serve as a hardener, and about 10-200 phr of filler.
  • Resin A hydrocarbon resin backbone
  • the hydrocarbon resin used in the examples of the invention was prepared as followed.
  • a C5 monomer stream of piperylene, amylene, isoprene was introduced to 0.2 wt% AlCb, a Lewis acid catalyst, to undergo rapid polymerization at a reaction temperature of 0°C to form 1, 2 or 1, 4 addition product.
  • the polymerization can be controlled to produce more 1, 2 or 1, 4 product with the proper choice of Lewis acid, concentration of Lewis Acid, and reaction temperature.
  • the polymerization was quenched with isopropanol and the product was distilled with nitrogen to a resin yield of 30%. All manipulations were performed under inert atmosphere in a nitrogen-purged glove box.
  • Resin A was then functionalized with various polar functional groups (epoxy, hydroxyl, acetate, and silicon), as described below.
  • Resin B Epoxy-functionalized resin
  • Resin C Hydroxyl-functionalized resin
  • the following comparative example describes a methodology to prepare oligohydroxy cyclopentadiene.
  • a 20 mL vial was charged with a solution of oligocyclopentadiene resin (56 mg, 0.2 mmol), followed by anhydrous THF (2 mL), and BH3 » THF (0.4 mL, 1 M, 0.5 mmol), and the mixture was allowed to stir at ambient temperature (about 23.5°C).
  • the mixture as diluted with aqueous KOH (0.5 mL, 3 M), and 0.1 mL of 30% H2O2 was added.
  • the inventors observed complete conversion of the olefinic groups to alcohols in both oligopiperylene resins and oligocyclopentadiene resins under mild conditions using BH3 » THF, and subsequent oxidation using H2O2 under alkaline conditions without intermediate purification. NMR confirms complete conversion, and does not suggest any unwanted side reactions.
  • Resin D Acetate-functionalized resin
  • Resin E Silicon-functionalized resin
  • This invention describes synthesis of polar functional hydrocarbon tackifiers via post polymerization route.
  • the epoxy, hydroxyl and acetate functional tackifiers will improve compatibility and thus provides better adhesion, corrosion prevention, and water resistance in the fields of coatings, adhesives, and sealants.
  • the silicone functional hydrocarbon tackifiers can be used for high performance tire treads.
  • the invention is not limited to the use of epoxy, hydroxyl, acetate, and silicon functional groups.
  • compositions of the invention may be extruded, compression molded, blow molded, injection molded, and laminated into various shaped articles including fibers, films, laminates, layers, industrial parts such as automotive parts, appliance housings, consumer products, packaging, and the like.
  • compositions comprising the resin are useful in components for a variety of tire applications such as truck tires, bus tires, automobile tires, motorcycle tires, off- road tires, aircraft tires, and the like. Such tires can be built, shaped, molded, and cured by various methods which are known and will be readily apparent to those having skill in the art.
  • the compositions may be fabricated into a component of a finished article for a tire.
  • the component may be any tire component such as treads, sidewalls, chafer strips, tire gum layers, reinforcing cord coating materials, cushion layers, and the like.
  • the composition may be particularly useful in a tire tread.
  • compositions comprising the resin of the present invention are useful in a variety of applications, particularly tire curing bladders, inner tubes, air sleeves, hoses, belts such as conveyor belts or automotive belts, solid tires, footwear components, rollers for graphic arts applications, vibration isolation devices, pharmaceutical devices, adhesives, caulks, sealants, glazing compounds, protective coatings, air cushions, pneumatic springs, air bellows, accumulator bags, and various bladders for fluid retention and curing processes. They are also useful as plasticizers in rubber formulations; as components to compositions that are manufactured into stretch- wrap films; as dispersants for lubricants; and in potting and electrical cable filling and cable housing materials.
  • compositions comprising the resin may also be useful in molded rubber parts and may find wide applications in automobile suspension bumpers, auto exhaust hangers, and body mounts. In yet other applications, compositions of the invention are also useful in medical applications such as pharmaceutical stoppers and closures and coatings for medical devices.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un procédé de préparation d'une composition de résine fonctionnalisée par un groupe polaire comprenant les étapes de (A) mise en contact d'un squelette polymère avec un fragment réactif pour obtenir une composition de résine fonctionnalisée par un groupe polaire, où le squelette polymère est dérivé d'une charge comprenant une quantité inférieure ou égale à environ 35 % en poids de composants dérivés du pipérylène ; une quantité inférieure ou égale à environ 10 % en poids de composants dérivés de l'amylène ; une quantité inférieure ou égale à environ 10 % en poids de composants dérivés de l'isoprène ; une quantité inférieure ou égale à environ 55 % en poids de paraffines non réactives ; et des résines homopolymères ou copolymères C9, en présence d'un catalyseur de type Friedel-Crafts ou d'acide de Lewis ; et de (B) récupération de la composition de résine fonctionnalisée par un groupe polaire.
PCT/US2018/015370 2017-03-08 2018-01-26 Résine hydrocarbonée fonctionnalisée par un groupe polaire par modification post-réacteur Ceased WO2018164777A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR1020197026404A KR20190120768A (ko) 2017-03-08 2018-01-26 후-반응기 개질을 통한 극성 작용화된 탄화수소 수지
CN201880026318.3A CN110770263A (zh) 2017-03-08 2018-01-26 经由反应器后改性的极性官能化烃树脂
EP18704383.1A EP3592785A1 (fr) 2017-03-08 2018-01-26 Résine hydrocarbonée fonctionnalisée par un groupe polaire par modification post-réacteur
SG11201908246W SG11201908246WA (en) 2017-03-08 2018-01-26 Polar functionalized hydrocarbon resin via post-reactor modification
JP2019548678A JP2020514501A (ja) 2017-03-08 2018-01-26 ポストリアクター修飾を経た極性官能化炭化水素樹脂
US16/491,260 US20200010595A1 (en) 2017-03-08 2018-01-26 Polar Functionalized Hydrocarbon Resin Via Post-Reactor Modification

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201762468535P 2017-03-08 2017-03-08
US62/468,535 2017-03-08
EP17165978 2017-04-11
EP17165978.2 2017-04-11

Publications (1)

Publication Number Publication Date
WO2018164777A1 true WO2018164777A1 (fr) 2018-09-13

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WO (1) WO2018164777A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2833747A (en) * 1954-10-20 1958-05-06 Fmc Corp Epoxidized hydrocarbon resins
US3376362A (en) * 1965-04-13 1968-04-02 Exxon Research Engineering Co Carboxylation of hydrocarbon resins
US3427293A (en) * 1967-10-27 1969-02-11 Exxon Research Engineering Co Phosphorylation of hydrocarbon resins
WO2002004530A2 (fr) * 2000-07-06 2002-01-17 Eastman Chemical Resins, Inc. Resines d'hydrocarbure en c5 liquide maleate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2833747A (en) * 1954-10-20 1958-05-06 Fmc Corp Epoxidized hydrocarbon resins
US3376362A (en) * 1965-04-13 1968-04-02 Exxon Research Engineering Co Carboxylation of hydrocarbon resins
US3427293A (en) * 1967-10-27 1969-02-11 Exxon Research Engineering Co Phosphorylation of hydrocarbon resins
WO2002004530A2 (fr) * 2000-07-06 2002-01-17 Eastman Chemical Resins, Inc. Resines d'hydrocarbure en c5 liquide maleate

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